Sodium Chloride → HCID 23508391, compound

HRID 1883665Notes

Reaction equation

HRID 1883665 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[S:15](Cl)(=[O:18])(=[O:17])[NH2:16].[Cl-].[Na+]>CN(C)C(=O)C>[S:15](=[O:18])(=[O:17])([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:15](=[O:18])(=[O:17])[NH2:16])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)[NH2:16]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 145654-Amino-4'-hydroxybiphenylHCID 24499Chlorosulfamic acid

Product 1

HCID 23508391HCID 23508391, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

43 mg of 4′-aminobiphenyl-4-ol was dissolved in 0.7 ml of N,N-dimethylacetamide, and 107 mg of sulfamoyl chloride was added thereto under cooling with ice, followed by stirring at room temperature for 2.4 hours. After the reaction mixture was poured into a saturated aqueous solution of sodium chloride, the product was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the resulting crude product was purified by TLC (using a 17:10 mixture of chloroform and tetrahydrofuran as the developing solvent) to obtain 42 mg of 4′-(sulfamoylamino)biphenyl-4-yl sulfamate.

Workup

  1. temperatureunder cooling with ice
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe resulting crude product was purified by TLC (
  7. additiona 17:10 mixture of chloroform and tetrahydrofuran as the developing solvent)

Sources & evidence

ORD record
ord-ef98ee2eccfa46818902287337bf98a7
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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